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After Emma finds her college boyfriend's engraved watch at a vintage jewelry shop, her sister Bronwyn believes it is a sign, and decides to secretly play Cupid by sending Emma to the same bed and breakfast in Vermont that Fletcher is staying at one week before Christmas. However, upon arrival, Emma is not only shocked to bump into her first love after all these years, but also his vivacious daughter. Throughout the week, the two fight their feelings for one another as they plan a Christmas Eve show in hopes of saving the local theater.